Pyrrolidine → 6-(2-Methyl-6-(phenyl(pyrrolidin-1-yl)methyl)phenyl)-3-morpholinoquinolin-2-amine

HRID 1028952Notes

Reaction equation

Cl.Cl[CH:3]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([NH2:21])[C:15]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[CH:14]2.[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>C(#N)C>[CH3:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:3]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:5]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([NH2:21])[C:15]([N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1)=[CH:14]2

Participants

Conditions

Temperature: 100 °C

Procedure

A Smith synthesizer vial containing 6-(2-(chloro(phenyl)methyl)-6-methylphenyl)-3-morpholinoquinolin-2-amine hydrochloride (0.050 g, 0.104 mmol) and ACN (0.42 mL) was treated with pyrrolidine (0.052 mL, 0.624 mmol). The reaction mixture was warmed to 100° C. for 1 h and then allowed to cool to RT. The mixture was purified by HPLC (1-70% ACN/H2O, TFA modifier). A single clean fraction was treated with NH4OH and concentrated to ¼ volume. The resulting precipitate was collected and dried under a stream of N2 to afford 6-(2-methyl-6-(phenyl(pyrrolidin-1-yl)methyl)phenyl)-3-morpholinoquinolin-2-amine. MS (ESI, pos. ion) m/z: 479 (M+1).

Workup

temperatureto cool to RT
customThe mixture was purified by HPLC (1-70% ACN/H2O, TFA modifier)
additionA single clean fraction was treated with NH4OH
concentrationconcentrated
customThe resulting precipitate was collected
dry with materialdried under a stream of N2

Sources & evidence

ORD record: ord-13076580986048f4863364a55ab733d7
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735384B2

Reaction notes

Loading…